Synthesis and evaluation of in vitro anticancer activity of some novel isopentenyladenosine derivatives

Roberta Ottria, Silvana Casati, Ada Manzocchi, Erika Baldoli, Massimo Mariotti, Jeanette A M Maier, Pierangela Ciuffreda

Research output: Contribution to journalArticlepeer-review

Abstract

The present study describes the synthesis, the characterization and the evaluation of some derivatives of N6-isopentenyladenosine on T24 human bladder carcinoma cells. In particular we have modified the hydroxyl groups in the ribose moiety, the position of the isopentenyl chain in the purine ring and the base moiety. The structures of the compounds were confirmed by standard studies of NMR, MS and elemental analysis. We here show that only two derivatives, 1-(3-methyl-2-butenylamino)-9-(3′-deoxy-β-d-ribofuranosyl)-purine hydrobromide and 2-amino-6-(3-methyl-2- butenylamino)-9-(β-d-ribofuranosyl)-purine, inhibit the growth of T24 cells, although to a lower extent than N6-isopentenyladenosine. We conclude that the integrity of ribosidic and purine moiety and the N6 position of the chain are essential for maintaining the antiproliferative activity.

Original languageEnglish
Pages (from-to)4249-4254
Number of pages6
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number12
DOIs
Publication statusPublished - Jun 15 2010

Keywords

  • Antitumor agents
  • Bladder carcinoma cells
  • Isopentenyladenosine
  • Modified nucleosides

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry
  • Medicine(all)

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